112345-60-5

Basic information

• Product Name: carbanicotinamide adenine dinucleotide
• Synonyms: carbanicotinamide adenine dinucleotide
• CAS NO: 112345-60-5
• Molecular Formula: C₂₂H₂₉N₇O₁₃P₂
• Molecular Weight: 661.452282
• Mol File: 112345-60-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: carbanicotinamide adenine dinucleotide(CAS DataBase Reference)
• NIST Chemistry Reference: carbanicotinamide adenine dinucleotide(112345-60-5)
• EPA Substance Registry System: carbanicotinamide adenine dinucleotide(112345-60-5)

Safety Data

• Hazardous Substances Data: 112345-60-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C22H29N7O13P2/c23-19-14-21(26-8-25-19)29(9-27-14)22-18(33)17(32)13(41-22)7-40-44(37,38)42-43(35,36)39-6-11-4-12(16(31)15(11)30)28-3-1-2-10(5-28)20(24)34/h1-3,5,8-9,11-13,15-18,22,30-33H,4,6-7H2,(H5-,23,24,25,26,34,35,36,37,38)/t11-,12-,13-,15-,16+,17-,18-,22-/m1/s1

Upstream product

• 98-92-0 nicotinamide 
• 53406-00-1 3-carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride 
• 85026-59-1 (-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane 
• 79200-54-7 methyl (1S,2R,3S,4R)-4-amino-2,3-dihydroxycyclopentane-1-carboxylate hydrochloride 
• 79200-55-8 (1R,4S,5R,6S)-5,6-dihydroxy-2-azabicyclo[2.2.1]heptan-3-one 
• 132486-54-5 ((1R,2R,3S,4R)-4-(3-carbamoylpyridin-1-ium-1-yl)-2,3-dihydroxycyclopentyl)methyl hydrogen phosphate 
• 24558-92-7 N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 
• 102099-16-1 chlorure de (-)-aminocarbonyl-3-(hydroxymethyl-cis-4-dihydroxy-trans-2,3-cyclopentyl) 1-pyridinium 

Relevant articles and documents

Synthesis of carba-NAD and the structures of its ternary complexes with SIRT3 and SIRT5

Carba-NAD is a synthetic compound identical to NAD except for one substitution, where an oxygen atom adjacent to the anomeric linkage bearing nicotinamide is replaced with a methylene group. Because it is inert in nicotinamide displacement reactions, carba-NAD is an unreactive substrate analogue for NAD-consuming enzymes. SIRT3 and SIRT5 are NAD-consuming enzymes that are potential therapeutic targets for the treatment of metabolic diseases and cancers. We report an improved carba-NAD synthesis, including a pyrophosphate coupling method that proceeds in approximately 60% yield. We also disclose the X-ray crystal structures of the ternary complexes of SIRT3 and SIRT5 bound to a peptide substrate and carba-NAD. These X-ray crystal structures provide critical snapshots of the mechanism by which human sirtuins function as protein deacylation catalysts.